1,1,1-trimethyl-N-((trimethylsilyl)oxy)silylamine → N-((S)-3-(1H-indol-3-yl)-1-(3-(isoquinolin-6-yl)isoxazol-5-ylamino)propan-2-yl)-4-nitrobenzenesulfonamide

HRID 598855노트

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HRID 598855 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH2:12][N:13]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]=[N:30][CH:29]=[CH:28]4)[CH:21]=2)C(=O)OCC=C)=[CH:2]1.C[Si](C)(C)NO[Si](C)(C)C>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:35][S:36]([C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)(=[O:37])=[O:38])[CH2:12][NH:13][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]=[N:30][CH:29]=[CH:28]4)[CH:21]=2)=[CH:2]1

참가 물질

5

반응물 2

HCID 898151,1,1-trimethyl-N-((trimethylsilyl)oxy)silylamineHCID 67062570HCID 67062570, 화합물

생성물 1

HCID 67062590N-((S)-3-(1H-indol-3-yl)-1-(3-(isoquinolin-6-yl)isoxazol-5-ylamino)propan-2-yl)-4-nitrobenzenesulfonamide수율 86.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of allyl(S)-3-(1H-indol-3-yl)-2-(4-nitrophenylsulfonamido)propyl(3-(isoquinolin-6-yl)isoxazol-5-yl)carbamate (100 mg, 153 μmol) in 2.5 mL of DCM was added Pd(PPh3)4 (5.3 mg, 4.6 μmol) and N,O-bis(trimethylsilyl)hydroxylamine (27 mg, 153 μmol). The mixture was stirred for 15 minutes and was then quenched with 2.5 mL saturated aqueous NH4Cl and the biphasic mixture was stirred for 2 hours. The mixture was then partitioned and the aqueous portion was extracted twice with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative LC to give N-((S)-3-(1H-indol-3-yl)-1-(3-(isoquinolin-6-yl)isoxazol-5-ylamino)propan-2-yl)-4-nitrobenzenesulfonamide (75 mg, 86% yield). MS m/z: 569 (M+1).

후처리

  1. customwas then quenched with 2.5 mL saturated aqueous NH4Cl
  2. stirringthe biphasic mixture was stirred for 2 hours
  3. customThe mixture was then partitioned
  4. extractionthe aqueous portion was extracted twice with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative LC

출처 및 근거

ORD 기록
ord-716ab312ebf94defb21729ae7ad86230
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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